When I was a kid playing chess with my dad, he sometimes would offer me hints on some good moves. I would never make those moves. I would rather make other sub-optimal moves for the sake of not taking on his advices, believing that my eventual success—much rarer than I would hope—should be attributed solely to my own volition and endeavor.

I find such irrational rationale the perfect metaphor for many adventures in my life. I preferred to learn things the hard way by myself and I did. It took me a while to realize the story I touted that I was a self-made man could not have been more misleading. Despite all my trials and errors, I would have come nowhere close to where I am had I not had the help from my parents, friends, advisors, and colleagues.

Hence, though I would never stop experimenting, I started to seek advices from all sorts of venues. Many lessons need not be learned the hard way. If you share my goal of personal and career growth, here is a collection of wisdom I gained over the years from either misadventures of my own or people I admire and respect.

Learning is Compounding

Prioritize learning over pay. At the start of one’s career, the pay differences among offers are negligible after taxes. At 22, your largest investment capital is your time. Invest early and continuously in yourselves to leverage the compounding effects, which apply to both learning and career. Your personal growth and career growth is not a forcing function that only increases with time—you are not growing but just getting older if you are essentially doing the same job for many years. Inductively, your next opportunity directly relates to your current knowledge and experience. Optimize for growth to get the best opportunity, and the pay always follows.

We tend to massively underestimate the compounding returns of intelligence. As humans, we need to solve big problems. If you graduate Stanford at 22 and Google recruits you, you’ll work a 9-to-5. It’s probably more like an 11-to-3 in terms of hard work. They’ll pay well. It’s relaxing. But what they are actually doing is paying you to accept a much lower intellectual growth rate. When you recognize that intelligence is compounding, the cost of that missing long-term compounding is enormous. They’re not giving you the best opportunity of your life. Then a scary thing can happen: You might realize one day that you’ve lost your competitive edge. You won’t be the best anymore. You won’t be able to fall in love with new stuff. Things are cushy where you are. You get complacent and stall.

– Stephen Cohen, Co-founder and Executive VP of Palantir

Join Companies on the Breakout Trajectory

Your scope and impact will be much larger than what your title suggests. You will work with the smartest people on the latest technologies without servicing legacy baggage. You will likely work with open-source software (OSS) that grants you directly transferable skills. Your patches back to the OSS community give you unparalleled external visibility. Companies on the breakout trajectory entail less risk than do seed-round startups struggling to find product-market fit and yet more upside than established counterparts.

The company itself will be focusing on exponential growth in business and people. There will always be more work than people on it and fewer politics—hardly fights over interesting projects or he-said-she-said nonsense. In the future, having this company on your resume gives you more credit than you deserve. Being at Paypal around 2000, Google in 2005, and Facebook in 2010 is worth more than any advanced degree will buy in this market.

Career takes care of itself. Your career growth is the superposition of your personal growth and company growth. Companies often prefer to promote from within than to hire external talent to preserve the culture and spare knowledge transfer. With your large scope and impact and expanding headcounts of all levels in all departments, promotion is fast. Your experience means a lot externally as well. Everyone wants to recruit from successful companies in the hope that people carry the lessons of success with them.

If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.

– Sheryl Sandberg, COO of Facebook

All our advice on Silicon Valley careers is based on a simple idea: that your choice of company trumps everything else. It’s more important than your job title, your pay or your responsibilities.

– Andy Rachleff, Executive Chairman of Wealthfront, Partner at Benchmark Capital

Prestige Matters But Can Be Manufactured

At first sight, prestige seems misplaced in Silicon Valley. I have trouble thinking of a more meritocratic industry than tech and engineering. Yet prestige still matters. At virtually every company, the hiring process biases towards respected colleges for the promise of rigorous curricula and talented students and from other elite companies, say FAANG.

Many desirable things that you want over the course of your career will be gated by mechanisms that favor folks with prestige. You can be justly upset by that fact, but upset is an insufficient catalyst for change, and ultimately you’ll have to develop your own prestige to gain access to those scarce opportunities and resources. Prestige makes everything more attainable: a universal lubricant.

– Will Larson, Head of Foundation engineering at Stripe

But fear not! Prestige can be manufactured. Promote yourselves with blogs, newsletters, podcasts, conference talks, and open-source contributions. Things get easier and compound over time. Your first few blogs may lead to column writing, which may lead to book writing invitation by publishers. Your youtube channel or podcasts enable you to talk on meetups and eventually conferences. All these will allow you to be discoverable by the next best opportunities in life.

Your Manager and Colleagues, Not Company, Determine 95% of Your Experience

Before taking the offer, talk to your future direct manager and colleagues and ask hard questions. Everyone has their style of working, and different teams have disparate prospects, focus, and dynamics. Try really understand what you are getting yourselves into and if this is the right opportunity for you. Here are some questions that I find helpful to uncover this information. For managers,

• Is this position open because the last person left or your team expanded?
• What are the projects that I will be working on? Who is the customer? Why is it more important than other backlog projects?
• How many reports do you have? How many of them are senior or staff? How long have they joined the company?
• What is your management style?
• What is the career outlook for this position? What is the next role that I can grow into? Has anyone done it?
• How would you help develop the career of your reports?

For colleagues,

• If you have the power, what is the one thing that you would like to change about this company?
• What projects are you working on? What do you like or dislike about them?
• How do you solve XYZ? I have used ABC before but I am interested to know why your team uses DEF.
• How do you like your team/manager?
• Tell me the workflow of your team from request gathering to production.
• Do you know your skip manager and vice versa?

You Get What You Put In

Be proactive at work. Help investigate outages even when you are not on call. Read code and documentations aggressively to understand how your and other systems work. Do not be limited by your sprint goal or responsibility. Fix the things that were a pain for everyone. Document tribal knowledge that you have acquired. Attend postmortems and ask questions. Review and comment on design documents and pull requests. In essence, you do more to get more.

People, Not Jobs, Last Forever

You will likely switch companies every few years, but the people in the industry are here for long. You take all the relationships you have built—good and bad ones—into your new adventures. Try to build good, lasting relationships. Pick the people you work with. Capable and affable coworkers can only accelerate your career. These are the group of people to put your name into referrals or to join your next undertaking.

Positive relationships enable serendipity, and serendipity is the source of the most interesting opportunities.

– Will Larson, Head of Foundation engineering at Stripe

Switch teams and companies every now and then, help in hiring and interviewing, offline engagements at conferences or meetups will grow your personal network.

Some Book Recommendations

• The Hard Thing About Hard Things
• The Mythical Man-Month
• The Last Lecture
• Site Reliability Engineering at Google
• How to Win Friends & Influence People
• Difficult Conversations: How to Discuss What Matters Most